How to name organic compounds using the IUPAC rules In order to name organic compounds you must first

memorize a few basic names. These names are listed within the discussion of naming alkanes. In general, the base part of the name reflects the number of carbons in what you have assigned to be the parent chain. The suffix of the name reflects the type(s) of functional group(s) present on (or within) the parent chain. Other groups which are attached to the parent chain are called substituents.

lkanes ! saturated hydrocarbons The names of the straight chain saturated hydrocarbons for up to a "# carbon chain are shown below. The names of the substituents formed by the removal of one hydrogen from the end of the chain is obtained by changing the suffi$ ! ane to !yl. Number of Carbons Name " methane # ethane % propane & butane ' pentane ( hexane ) heptane * octane + nonane ", decane "" undecane "# dodecane There are a few common branched substituents which you should memorize. These are shown below.

-ere is a simple list of rules to follow. .ome e$amples are given at the end of the list.

". Identify the longest carbon chain. This chain is called the parent chain. #. Identify all of the substituents (groups appending from the parent chain). %. /umber the carbons of the parent chain from the end that gives the substituents the lowest numbers. 0hen compairing a series of numbers, the series that is the 1lowest1 is the one which contains the lowest number at the occasion of the first difference. If two or more side chains are in e2uivalent positions, assign the lowest number to the one which will come first in the name. &. If the same substituent occurs more than once, the location of each point on which the substituent occurs is given. In addition, the number of times the substituent group occurs is indicated by a prefi$ (di, tri, tetra, etc.). '. If there are two or more different substituents they are listed in alphabetical order using the base name (ignore the prefi$es). The only prefi$ which is used when putting the substituents in alphabetical order is iso as in isopropyl or isobutyl. The prefi$es sec! and tert! are not used in determining alphabetical order e$cept when compared with each other. (. If chains of e2ual length are competing for selection as the parent chain, then the choice goes in series to3 a) the chain which has the greatest number of side chains. b) the chain whose substituents have the lowest! numbers. c) the chain having the greatest number of carbon atoms in the smaller side chain. d)the chain having the least branched side chains. ). cyclic (ring) hydrocarbon is designated by the prefi$ cyclo- which appears directly in front of the base name.

In summary, the name of the compound is written out with the substituents in alphabetical order followed by the base name (derived from the number of carbons in the parent chain). 4ommas are used between numbers and dashes are used between letters and numbers. There are no spaces in the name. -ere are some

e$amples3

lkyl halides The halogen is treated as a substituent on an alkane chain. The halo! substituent is considered of e2ual rank with an alkyl substituent in the numbering of the parent chain. The halogens are represented as follows3 5 4l 6r I -ere are some e$amples3 fluoro! chloro! bromo! iodo!

lkenes and lkynes ! unsaturated hydrocarbons 7ouble bonds in hydrocarbons are indicated by replacing the suffi$ -anewith -ene. If there is more than one double bond, the suffi$ is e$panded to include a prefi$ that indicates the number of double bonds present ( -adiene, -atriene, etc.). Triple bonds are named in a similar way using the suffi$ -yne. The position of the multiple bond(s) within the parent chain is(are) indicated by placing the number(s) of the first carbon of the multiple bond(s) directly in front of the base name. -ere is an important list of rules to follow3

". The parent chain is numbered so that the multiple bonds have the lowest numbers (double and triple bonds have priority over alkyl and halo substituents). #. 0hen both double and triple bonds are present, numbers as low as possible are given to double and triple bonds even though this may at times give 1!yne1 a lower number than 1!ene1. 0hen there is a choice in numbering, the double bonds are given the lowest numbers. %. 0hen both double and triple bonds are present, the !en suffi$ follows the parent chain directly and the !yne suffi$ follows the !en suffi$ (notice that the e is left off, !en instead of !ene). The location of the double bond(s) is(are) indicated before the parent name as before, and the location of the triple bond(s) is(are) indicated between the !en and !yne suffi$es. .ee below for e$amples. &. 5or a branched unsaturated acyclic hydrocarbon, the parent chain is the longest carbon chain that contains the maximum number of double and triple bonds. If there are two or more chains competing for selection as the parent chain (chain with the most multiple bonds), the choice goes to (") the chain with the greatest number of carbon atoms, (#) the 8 of carbon atoms being e2ual, the chain containing the ma$imum number of double bonds. '. If there is a choice in numbering not previously covered, the parent chain is numbered to give the substituents the lowest number at the first point of difference. -ere are some e$amples3

lcohols lcohols are named by replacing the suffi$ -ane with -anol. If there is more than one hydro$yl group (!O-), the suffi$ is e$panded to include a prefi$ that indicates

the number of hydro$yl groups present (-anediol, -anetriol, etc.). The position of the hydro$yl group(s) on the parent chain is(are) indicated by placing the number(s) corresponding to the location(s) on the parent chain directly in front of the base name (same as alkenes). -ere is an important list of rules to follow3 ". The hydro$yl group takes precedence over alkyl groups and halogen substituents, as well as double bonds, in the numbering of the parent chain. #. 0hen both double bonds and hydro$yl groups are present, the !en suffi$ follows the parent chain directly and the !ol suffi$ follows the !en suffi$ (notice that the e is left off, !en instead of !ene). The location of the double bond(s) is(are) indicated before the parent name as before, and the location of the hydro$yl group(s) is(are) indicated between the !en and !ol suffi$es. .ee below for e$amples. gain, the hydro$yl gets priority in the numbering of the parent chain. %. If there is a choice in numbering not previously covered, the parent chain is numbered to give the substituents the lowest number at the first point of difference. -ere are some e$amples3

9thers :ou are only e$pected to know how to name ethers by their commmon names. The two alkyl groups attached to the o$ygen are put in alphabetical order with spaces between the names and they are followed by the word ether. The prefi$ di! is used if both alkyl groups are the same. -ere are some e$amples3

ldehydes ldehydes are named by replacing the suffi$ -ane with -anal. If there is more than one !4-O group, the suffi$ is e$panded to include a prefi$ that indicates the number of !4-O groups present (-anedial ! there should not be more than # of these groups on the parent chain as they must occur at the ends). It is not necessary to indicate the position of the !4-O group because this group will be at the end of the parent chain and its carbon is automatically assigned as 4!". -ere is an important list of rules to follow3 ". The carbonyl group takes precedence over alkyl groups and halogen substituents, as well as double bonds, in the numbering of the parent chain. #. 0hen both double bonds and carbonyl groups are present, the !en suffi$ follows the parent chain directly and the !al suffi$ follows the !en suffi$ (notice that the e is left off, -en instead of !ene). The location of the double bond(s) is(are) indicated before the parent name as before, and the !al suffi$ follows the !en suffi$ directly. ;emember it is not necessary to specify the location of the carbonyl group because it will automatically be carbon 8". .ee below for e$amples. gain, the carbonyl gets priority in the numbering of the parent chain. %. There are a couple of common names which are acceptable as I<= 4 names. They are shown in the e$amples at the end of this list but at this point these names will not be accepted by the computer. 9ventually they will be accepted. &. If there is a choice in numbering not previously covered, the parent chain is numbered to give the substituents the lowest number at the first point of difference. -ere are some e$amples3

 >etones >etones are named by replacing the suffi$ -ane with -anone. If there is more than one carbonyl group (4?O), the suffi$ is e$panded to include a prefi$ that indicates the number of carbonyl groups present (-anedione, -anetrione, etc.). The position of the carbonyl group(s) on the parent chain is(are) indicated by placing the number(s) corresponding to the location(s) on the parent chain directly in front of the base name (same as alkenes). -ere is an important list of rules to follow3 ". The carbonyl group takes precedence over alkyl groups and halogen substituents, as well as double bonds, in the numbering of the parent chain. #. 0hen both double bonds and carbonyl groups are present, the !en suffi$ follows the parent chain directly and the !one suffi$ follows the !en suffi$ (notice that the e is left off, -en instead of !ene). The location of the double bond(s) is(are) indicated before the parent name as before, and the location of the carbonyl group(s) is(are) indicated between the !en and !one suffi$es. .ee below for e$amples. gain, the carbonyl gets priority in the numbering of the parent chain. %. If there is a choice in numbering not previously covered, the parent chain is numbered to give the substituents the lowest number at the first point of difference. -ere are some e$amples3

4arbo$ylic cids 4arbo$ylic acids are named by counting the number of carbons in the longest continuous chain including the carbo$yl group and by replacing the suffi$ -ane of the corresponding alkane with -anoic acid. If there are two !4OO- groups, the suffi$ is e$panded to include a prefi$ that indicates the number of !4OO- groups present (-anedioic acid ! there should not be more than # of these groups on the parent chain as they must occur at the ends). It is not necessary to indicate the position of the !4OO- group because this group will be at the end of the parent chain and its carbon is automatically assigned as 4!".

-ere is an important list of rules to follow3 ". The carbo$yl group takes precedence over alkyl groups and halogen substituents, as well as double bonds, in the numbering of the parent chain. #. If the carbo$yl group is attached to a ring the parent ring is named and the suffi$ !carbo$ylic acid is added. %. 0hen both double bonds and carbo$yl groups are present, the !en suffi$ follows the parent chain directly and the !oic acid suffi$ follows the !en suffi$ (notice that the e is left off, -en instead of !ene). The location of the double bond(s) is(are) indicated before the parent name as before, and the !oic acid suffi$ follows the !en suffi$ directly. ;emember it is not necessary to specify the location of the carbo$yl group because it will automatically be carbon 8". .ee below for e$amples. gain, the carbo$yl gets priority in the numbering of the parent chain. &. There are several common names which are acceptable as I<= 4 names. They are shown in the e$amples at the end of this list butat this point these names will not be accepted by the computer. 9ventually they will be accepted. '. If there is a choice in numbering not previously covered, the parent chain is numbered to give the substituents the lowest number at the first point of difference. -ere are some e$amples3

 9sters .ystematic names of esters are based on the name of the corresponding carbo$ylic acid. ;emember esters look like this3

The alkyl group is named like a substituent using the -yl ending. This is followed by a space. The acyl portion of the name (what is left over) is named by replacing the -ic acid suffi$ of the corresponding carbo$ylic acid with -ate. -ere are some e$amples3

mines :ou are only e$pected to know how to name amines by their common names . They are named like ethers, the alkyl (;) groups attached to the nitrogen are put in alphabetical order with no spaces between the names and these are followed by the word amine. The prefi$es di! and tri! are used if two or three of the alkyl groups are the same. /OT93 .ome books put spaces between the parts of the name, but we will not. 5ollow the e$amples. -ere are some e$amples3

.ummary of functional groups Functional group Prefix carbo$ylic acids none uffix !oic acid

aldehydes ketones alchols amines ethers fluorine chlorine bromine iodine

none !al none !one hydro$y! !ol amino! !amine alko$y! !ether fluoro! none chloro! none bromo! none iodo! none